So much of my musical inspiration has been drawn from Josh in the last few years, in fact, that when I played one of the first songs I wrote for my sister, she exclaimed that she didn’t know Ritter had written a song about so many of the places we’d been spending our summer vacations. To boot, the afternoon I spent in the Commodore with Josh, in addition to enjoying the show that night (despite it being already the third time seeing him in concert) provided a profound shift in my thinking about writing and performing music.

I was struck not only by the reaction the show brought out in myself – jubilation, revelry, and an unending grin that followed me home and into work the rest of the week – but also the appreciation I was gaining for just what it was I saw Josh doing from the stage: breathing life into the room and connecting to people through the sheer force of his love for what he had forged with his own imagination and enthusiasm.

It was a glimpse of what I would later hear Bruce Springsteen describe as music’s ability to allow for the creation of “a transformative self.“

By sharing what he loved to do with others. Could it be that easy?

Well… not entirely. But imagine my appreciation to find Josh’s series of blog posts laying bare his path to the Commodore stage that night. Here are a series of posts from 2010 wherein he offers advice for Making a Life in Music, from buying yourself a notebook, to sharing a tour bus with Joan Baez.

To strain a metaphor to breaking, Death is the enigma and Art is the engine we build to decipher it. Each of us makes Art as a way to understand human problems (Love, War, God, Death, Sandwiches) of great complexity. While we go about our day-to-day lives we are constantly feeding information into the engines we create for ourselves, gaining insight and slowly solving the enigma. Art is one such engine.

Goals are very different birdies. Even the words sound different. Aspiration, that airy puff of breath, is such a suave word, soaring high above its stolid, plunkier cousin, goal. You can even tell, by the sound of the two words, which one gets the work done. A lot of people want, for some reason, a tour bus. They dream about it and never sit down to figure out, actually, how they are going to get that tour bus. Aspirations are good, nice things to have, don’t get me wrong, but they’re the pie in the sky, and if you want pie, you’re gonna need goals.

Open mics are fun, but treat them professionally and you will learn about how to be a professional. Make them your second job. Attend them diligently, meet people, keep your instrument in tune, and in the words of a famous open mic superstar, learn your song well before you start singing. Pay attention to what the crowd needs, always have a mailing list with you, and if you have recordings, bring them along. It may take a few years and more than a few late nights before you’re ready to progress on from open mics, but you’re starting at the bottom and these will be some of the most memorable, beautiful, challenging times that you’ll have in your entire career, and I guarantee you’ll never forget them.

[Artists] should look for someone who thinks about their art as much as they do. Someone who sends them TOO MANY emails / texts / ideas about their music. They should look for the person in their life who’s pushing them. Someone who’s a good listener but who isn’t a tool or a yes-man. There’s someone in their life who’s curious. Someone who’s a little bit competitive. Someone they can talk music with and someone who is ready to work hard.

Artists are empathetic people. They have a great capacity to feel the emotions of others. As such, they are easily able to imagine, rightly or wrongly, what it must be like to be someone else; someone more popular, more good-looking, funnier, wealthier. It is this ability to imagine that gives us the power to do create, but empathy is (again alas) threaded through with strong streaks of jealousy. A little imagination can go a long way towards envisioning what our life would be like if only such-and-such happened to us instead of to the other guy. We imagine ourselves in his place, and those grapes he is eating no doubt taste far better than these sour ones we ended up with. Well, imagining yourself in his place isn’t bad as long as you do something constructive with it.

If the open mic is where you first learn to play your songs in front of people, the opening set is where you’ll start to learn your place in the music business ecosystem. Here is where you’ll really be tested and where you’ll find out your capacity to make the best of demanding situations. The benefits of being on the bill are great, but the demands are also great, and your ability to conduct yourself professionally (and optimistically) is equal to the opportunity you’re being given.

The best stuff about living a life in music is the stuff that comes to you unexpectedly. Nothing about your life can be planned so well that the best stuff won’t find its way in and change everything. The sound system will break and you’ll be forced to play without amplification. There will be a storm and you’ll have no electricity. You’ll mess up your place in the song and a whole new way to play it will suddenly come to you. Something in your life will change and you’ll realize just how important the other parts are.